Methanol → 7-METHOXY-8-NITROQUINOLINE

HRID 34450Notes

Reaction equation

HRID 34450 reaction equation
[Na].Cl[C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.[CH3:23][OH:24]>>[CH3:23][O:24][C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 4597147-Chloro-8-nitroquinolineHCID 5360545Sodium

Product 1

HCID 112064927-METHOXY-8-NITROQUINOLINE

Procedure

To a freshly prepared solution of sodium (16.5 g, 0.720 mol) in methanol (750 mL) was added 7-chloro-8-nitroquinoline (18.72 g, 0.090 mol) [E. Fourneau, M. and Mme. Trefouel, and A. Wancolle, Bull. Soc. Chim. Fr., 47, 738(1930); A. K. Sen, N. K. Ray, V. P. Basu, J. Sci. Ind. Res., 11B, 322(1952) (C.A. 47, 4339e)]. This mixture was refluxed for 3 hr, cooled, then filtered to collect the precipitated solid. This solid was slurried in water, collected on a filter and dried; yield, after recrystalllization from toluene, 16.12 g (88%); mp 178°-178.5°: Anal. Calcd for C10H8N2O3 : C, 58.82; H, 3.95; N, 13.72. Found: C, 58.66; H, 3.87; N, 13.69.

Workup

  1. temperatureThis mixture was refluxed for 3 hr
  2. temperaturecooled
  3. filtrationfiltered
  4. customto collect the precipitated solid
  5. customcollected on
  6. filtrationa filter
  7. customdried
  8. customyield

Sources & evidence

ORD record
ord-22bc184f94144185a0de51248b064a14
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Reaction notes

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